


Let You Undress My Mind

by xLoveMx



Category: Critical Role (Web Series)
Genre: F/M, Fluff, Smut, Vaginal Fingering, Vaginal Sex, Widojest - Freeform, laura cannot write pwp, this is so soft you guys
Language: English
Status: Completed
Published: 2020-09-18
Updated: 2020-09-18
Packaged: 2021-03-07 21:22:17
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,238
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26534290
Author URL: https://archiveofourown.org/users/xLoveMx/pseuds/xLoveMx
Summary: There was a sudden shift as they moved, and then gravity got the better of them.
Relationships: Jester Lavorre/Caleb Widogast
Comments: 12
Kudos: 156





	Let You Undress My Mind

**Author's Note:**

> Hello and welcome to: Laura is physically incapable of writing Porn Without Plot! xD
> 
> Seriously. You guys. This is so soft. *cries*
> 
> Enjoy x

It wasn’t Jester’s fault that she couldn’t get the image of Caleb in her bed out of her head. In fact, she had found it quite hard to get Caleb out of her head in general these past few weeks. She had always admired him, been in awe of the spell he was able to do, but there was just something different about the way he made her feel, especially when he went out of his way to make her smile with his creations.

For a while Jester had thought that it was normal, that he’d be doing it for anyone, and the truth was: He probably would if he was asked to, but all these decorations and lights at Traveler Con had been done unprompted. He had gone and made her smile, supported her when she had needed it and trusted her to make the right calls.

Then the butterflies had started coming, but she hadn’t thought much of it either, because she’s had a crush before, and it had felt entirely different. With Fjord everything had been exciting and new and it also a little fun to see him squirm whenever her affection had shifted towards him, but with Caleb things weren’t like that. Everything was warm and safe and there was that overwhelming need to know more about him. The need for him to trust her enough to tell her what he was going through. She had learned to be patient though, so when he had finally opened up, whether it had been urged on by the fear of Trent using his knowledge of Caleb’s past against him or not, Jester was glad that this wasn’t something that stood between them anymore.

She had a slight suspicion that the others had known already, but she didn’t blame him, how could she? She had, after all, spent the better part of this journey pretending she was fine, because she didn’t want people to see how vulnerable she really was.

The memory of Caleb’s arms wrapping around her, reciprocating the hug she had given him, surfaced and Jester suddenly felt her chest tighten. Whatever tomorrow was going to bring, she knew it wasn’t going to be pleasant. They were all absolutely ready to murder Trent, no questions asked, but despite everyone seemingly hating him she was sure that murdering a member of the Assembly, no matter how despised he was, would have repercussions.

Biting her lip Jester huffed out a sigh, before sitting up in bed eventually and tracing her fingers in the air for a moment.

_“Caleb? Are you still awake? Can you come over to my room for a moment?”_ Of course Jester could have gone over to knock on his door, but if he didn’t want any company then she’d feel stupid for even showing up, this way he would be able to pretend like he was already asleep.

_“Jester. Are you okay? I’ll be right over,”_ He sounded almost concerned as his response came through, and for a moment she felt bad about making him worry, especially since this time around it was her who was supposed to be worried, but it was all washed away by the butterflies in her stomach when she heard a knock on her door just a moment later.

“It’s open!” She called, swinging her legs out of bed and watching as the door was carefully pushed open and Caleb slipped inside. He was dressed in simple pants and his long sleeve shirt, with his hair pulled into the familiar ponytail. Jester had assumed he’d still be up, either reading or maybe just worrying about what tomorrow would bring.

“Everything alright?” She felt her heart miss a beat by just hearing his voice and was suddenly glad that the room was only dimly lit, so he couldn’t see the blush rising to her cheeks.

“Yeah...I just wanted to check on you, you know, today was...quite a day.” In fact, it felt like at least a week had passed since they had returned from Rumblecusp, gone to Rexxentrum and Caleb had received that fateful letter that had caught all of them a little off guard.

“I’m not sure that covers it,” Caleb found himself nodding and Jester watched as he sat down next to her, the mattress dipping just a little.

“Yeah...I mean.” Frowning ever so slightly, she turned towards him, searching his face for any kind of worry or maybe even fear. “I know you said he probably won’t come after you, and it’s unlikely he’ll come here but...I don’t want you to sleep alone.”

_I want to be close to you,_ was what she really wanted to say, but even though it made sense in her head, Jester found that it was much harder to put into actual words.

“Well I could ask Fjord if he doesn’t mind rooming with me for the night if that makes you feel better,” Caleb replied, but Jester was quick to interject.

“No!” Her hand instinctively reached out, covering his in the space between them. “No, I mean. You can stay here.” For a split second she was sure that he was going to say no. She had been wondering, trying not to let herself believe that him coming up with all these spells for her meant something other than him helping out a friend. She didn’t want to end up disappointed again, like when she had assumed that he’d dance with her, only to then go and choose Beau and Fjord over her. The rational part of Jester’s brain told her that there had probably been a reason for it, because Caleb rarely did anything without a reason, but she still hadn’t been able to shake the feeling of jealousy.

There was no response as of now, just Caleb searching her eyes for something Jester couldn’t quite make out, so instead of saying anything else she simply pulled him down onto the bed, linking their fingers together.

Caleb went willingly, which had her heart stumbling again as they settled in beside each other. The bed was too small for them, and she could tell that Caleb’s feet were dangling over the edge as she used her free hand to pull the covers over them. Jester could feel her heart beating faster against her ribcage, and she was sure that, if she hadn’t been holding onto Caleb, her hand would have been shaking just a little.

She was wondering what to say next, or whether to say anything at all, when Caleb waved his free hand through the air, and a moment later the familiar light globes were floating upwards, partly illuminating the room, but mainly putting a spotlight on the mural that was only visible from their current point of view.  
“When did you paint that?” His voice was quiet and almost soothing, and Jester thought that really, she should be the one doing the soothing with how this day had gone, and yet she found a warmth spreading through her chest and her lips curved into a smile.

“I was...fifteen or sixteen, maybe? Sometimes the Traveler, well...Artagan, he couldn’t always be around to cheer me up, and sometimes it was hard to even get out of bed to look out the window,” These weren’t exactly memories Jester enjoyed looking back upon, but it was becoming a little easier now that she was traveling the world and had friends who supported her. Now that she had Caleb. “So...I painted the view from the window up there, so I would get to see the ocean even if I didn’t make it out of bed that day,” It felt oddly good to finally tell someone, because she had never wanted to worry her mother, and if Artagan had ever noticed the real reason she had painted the mural then he had never said anything about it. 

“I know you said we all...lie,” Caleb eventually spoke again, his eyes tracing over the painting, seemingly discovering something new every other second. “And...while I haven’t lied, I wasn’t entirely honest with you either. I...” A sigh escaped his lips and Jester shifted, angling her body towards his almost subconsciously. “Trent...he knows me better than most people, and Astrid and Eodwulf...well I don’t know how loyal they are to him, but...this could potentially come up and I don’t want him to use it against us,”

Jester’s heart was pounding in her chest as their eyes met, and she could tell that, whatever he was about to tell her, was accompanied by fear but also a sense of relief, like he had been carrying it around for a while.

“Jester...I...I love you. I thought about telling you so many times, but I always chickened out because...well, I don’t even know why. Or maybe I do...it doesn’t really matter. I might have never told you if it wasn’t for this, and I don’t want you to think that this has to mean anything. I...I care about you deeply and I couldn’t be more grateful to have you by my side, as a friend. I just don’t want him...” Jester, who’s brain had short circuited for just a moment at his words, didn’t let him finish. Once she remembered how to breathe, and move, her lips found his in a kiss.

There was a brief moment where Caleb seemed to be too shocked to do anything in return, the words he’d been meaning to say having died on his lips, but just before Jester could think that she might have made a mistake, arms came to wrap around her as he pulled her closer against himself.

Jester felt as if fireworks were exploding inside of her, leaving behind a warmth that filled her entirely as they kissed. Even her toes seemed to be curling as his fingers brushed her cheek and her own tangled in his hair.

There was a sudden shift as they moved, and then gravity got the better of them. Her bed really was too small, it barely fit her anymore, but to actually try and get two people in there might not have been the best idea. Caleb made an attempt to let go off her as he fell, but Jester only held on tighter as they tumbled to the floor.

For a moment there was nothing but silence as Jester landed on top of him, but before either of them could say anything a giggle escaped her lips and turned into full laughter, the vibration of it echoing against Caleb’s chest as he joined in.

There had been rare moments when he had let himself imagine a positive outcome to his confession, but this was definitely not how he had expected things to go. Reaching up to brush a strand of hair behind her ear, their laughter eventually died down until they were simply smiling at each other.

“We should probably...I mean if we want to...the bed in my room is bigger,” Caleb then muttered with a chuckle, and Jester’s eyes lit up a little as she got to her feet, pulling him along with her, their fingers intertwining. Peaking her head out into the corridor for a moment she made sure that no one was out there as she tugged Caleb down the hall, still giggling just a little.

He followed and when she looked back at him over her shoulder, she caught a brief glimpse of his smile, and it made her heart stutter again. Squeezing her hand, he let himself be pulled into the room he had occupied for the night, the door falling shut behind them.

Jester glanced around, finding that there were books left open on the floor, one of them with Frumpkin on top. The cat barely batted and eye as they entered, and Jester was quickly distracted by Caleb pulling her against him.

Her cheeks were flushed, and her stomach was doing flips as she pushed him towards the bed, lips finding his again. Part of her could have done this all night, just kissing him and enjoying the way his hands were warm against her cheeks, but there was also a part of her that wanted more. More of him. All of him, really.

Jester managed to undo his pants then and Caleb was surprisingly skilled in kicking them off as they stumbled onto the soft mattress.

Another giggle escaped her as she landed on top of him yet again, but this time gravity was kinder to them, or well, the bed was bigger anyways. Caleb’s hands were traveling up the back of her thighs and under the nightgown she was wearing, and Jester shivered.

“This okay?” He pulled back ever so slightly, his voice a little breathless. His ponytail had been messed up by her running her fingers through his hair and his lips were red from kissing, an image that made Jester’s cheeks flush again.

“Yeah...yeah...please...” She responded, diving back in for another kiss. There was just a tiny bit of friction she was getting from the way his leg was pressed up between her own and Jester couldn’t help but moan. It wasn’t nearly enough, but it was a start, so she ground her hips down, leaning into the touch as she felt her night gown being pushed up even further.

Caleb’s lips traveled over her jaw and down her neck while his hand snuck in between them, dipping into the waistband of her underwear. There was a brief moment of hesitation, as if to make sure that this was still alright, so Jester simply whispered “Yes,” and that was enough.

She gasped when his thumb brushed over her clit and Jester would have been a little embarrassed about how wet she already was, but two of his fingers slipped in with such easy that she rolled her hips to meet him, momentarily losing herself in the pleasure.

She could feel herself drifting closer and closer to the edge very quickly and one hand came up to push at his shoulder aimlessly.  
“Caleb...I...I w-want....” She moaned, the rest of her sentence getting cut off as he claimed her lips in another kiss and Jester desperately tried to hold on, but the pressure was building up so quickly that what little self-control she still possessed went out the window eventually. She came with a moan and Caleb’s name on her lips, hips stuttering against his hand before she eventually collapsed on top of him.

There was a moment of pure bliss as she slowly came back to herself, Caleb’s fingers brushing some hair, that had stuck to her face, away. “I want to...” She tried again, wriggling her hips and finding her lips curving into a grin as Caleb responded immediately. Biting his lips, he attempted to hold back a moan, but Jester kissed him again, flipping them over so she could pull him on top of her. He was by no means heavy, but there was a comfort to his weight pressing her down into the mattress, like a reminder that he was really there.

Pulling her underwear down the rest of the way and kicking it off, Jester leaned up to kiss him again, legs falling apart as she did. Her hands came to grab the hem of his shirt, pulling it over his head and tossing it off the bed before her fingers began tracing over naked skin, feeling the warmth radiate off of him.

“Caleb,” Jester whispered, pulling him down ever so slightly so her lips were right by his ear. “I want you inside of me...” Her words were followed by a moan as his lips found her neck again, teeth scraping over the skin just a little. Jester shivered, hands pushing down his underwear almost impatiently. Caleb’s cock was thick and long in her hand and despite the heat coiling at the base of her spine, Jester found herself blushing.

“You’re so beautiful,” Caleb’s voice broke through, followed by a moan as she gave a tentative stroke before his hand wrapped around hers, carefully guiding it between her legs. It was much more to take than the two fingers, but the initial burn was quickly replaced with a wave of pleasure as he was fully settled in, peppering her cheeks and shoulders with kisses to distract her.

It was slower than she had anticipated and when he pulled out almost all the way only to push back inside, she gasped, fingernails digging into his back as she pulled him close.

“Caleb...” She eventually moaned, “M-More...” At this point Jester wasn’t quite sure what she was asking for, but Caleb seemed to know regardless. He wrapped an arm around her to pull her closer, using the other to stabilize himself as he fell into a rhythm.

At some point Jester opened her eyes, not having realized that she had closed them at all, and caught a glimpse of Caleb, hair all messed up and falling into his face, with his pupils blown wide. It made he moan, and Jester shifted, wrapping her legs around his waist to pull him in even deeper with each thrust.

It was easy to spot that he was close, even through the haze. She had learned to watch him these past few months, catching herself looking at him ever so often whenever he twirled that wand between his fingers or traced his hands through the air for a spell. It had always been fascinating, but there was just something about the way his long fingers moved, especially now that they had been inside of her, that made Jester shiver.

“Caleb...Caleb...I...” The words had been on her tongue since he had spoken them, but then they had gotten lost in their kisses and the way her fingers had tangled in his hair. Sneaking a hand between them as Caleb sped up his thrusts, Jester pulled him close, resting their foreheads together. “I love you,”

She could feel herself clenching around him as she came, Caleb following suit as his hips began to stutter before he eventually collapsed on top of her, face buried into the crook of her neck.

“Say that again?” He eventually whispered, and Jester could feel his lips curved into a smile against her skin.

“I love you,” She responded, arms wrapping around him once more to pull him in closer as her eyes drifted shut. They didn’t move from their position for a while, eventually falling asleep after Caleb had cleaned them up.

When the sun rose over Nicodranas the next day, Jester found that she wasn’t as worried about the dinner as she had been the night before. Trent Ikithon might have been a powerful mage, but he didn’t have what Caleb had. Friendship, love and a family that would stand up for him, no questions asked.

Over breakfast everyone was quiet, but Jester swore that Marion was giving them a somewhat knowing, but soft, smile across the table and she could feel a warmth spreading through her chest as she snuck her hand into Caleb’s beneath the table.

_Whatever happens,_ she seemed to say, _it’s you and me._ And Caleb smiled in return, squeezing her hand as he nodded slowly, before pushing his leftover cinnamon pastry towards her, watching as Jester squealed in delight.


End file.
